S-Adenosylmethioninamine

S-Adenosylmethioninamine
Names
IUPAC name
S-(3-Aminopropyl)-S-methyl-5′-thioadenosin-5′-ium
Systematic IUPAC name
(3-Aminopropyl){[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}methylsulfanium
Other names
S-Adenosyl-(5′)-3-methylthiopropylamine
decarboxylated S-adenosyl methionine
decarboxy-S-adenosyl methionine
(5-Deoxy-5-adenosyl)(3-aminopropyl)methylsulfonium cation
Identifiers
CAS Number
3D model (JSmol)
Abbreviations dAdoMet, dc-SAM
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1 ☒N
    Key: ZUNBITIXDCPNSD-LSRJEVITSA-N ☒N
  • InChI=1/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/t8-,10-,11-,14-,24?/m1/s1
    Key: ZUNBITIXDCPNSD-LSRJEVITBK
SMILES
  • C[S+](CCCN)C[C@@H]1[C@H]([C@H]([C@@H](O1)n2cnc3c2ncnc3N)O)O
Properties
Chemical formula
 C14H23N6O3S+
Molar mass 355.43582 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

S-Adenosylmethioninamine is a substrate that is required for the biosynthesis of polyamines including spermidine, spermine, and thermospermine.[1] It is produced by decarboxylation of S-adenosyl methionine.

This reaction is catalyzed by S-adenosylmethionine decarboxylase.[2] The enzyme binds to S-adenosyl methionine (SAM) and removes the carboxyl group from the methionine. Once formed, S-adenosylmethioninamine donates its aminopropyl group to synthesize polyamines[3]. Polyamines are important for DNA stability, RNA function, and cell growth.[4]

See also

  • Adenosylmethionine decarboxylase (AMD1)
  • Spermidine synthase
  • Spermine synthase
  • Thermospermine synthase (ACAULIS5)

References

  1. ^ Takahashi, Taku; Kakehi, Jun-Ichi (2009-10-13). "Polyamines: Ubiquitous polycations with unique roles in growth and stress responses". Annals of Botany. 105 (1): 1–6. doi:10.1093/aob/mcp259. PMC 2794062. PMID 19828463.
  2. ^ Campbell, Mary K.; Farrell, Shawn O.; McDougal, Owen M. (2016). Biochemistry (9th ed.). Boston, MA: Cengage Learning. ISBN 978-1-305-96113-5.
  3. ^ Sirasunthorn, Nichanun; Jailwala, Anuj; Gerber, Anna; Comstock, Lindsay R. (2019-09-18). "Evaluation of N ‐Mustard Analogues of S ‐Adenosyl‐L‐methionine with Eukaryotic DNA Methyltransferase 1". ChemistrySelect. 4 (35): 10525–10531. doi:10.1002/slct.201902940. ISSN 2365-6549.
  4. ^ Takahashi, Taku; Kakehi, Jun-Ichi (2009-10-13). "Polyamines: Ubiquitous polycations with unique roles in growth and stress responses". Annals of Botany. 105 (1): 1–6. doi:10.1093/aob/mcp259. PMC 2794062. PMID 19828463.


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